CAS Number517-89-5
Synonyms5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methylpent-3-en-1-yl]-1,4-naphthoquinone; MFCD00075680; Shikonin; 5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-3-penten-1-yl]-1,4-naphthoquinone; (+)-Alkannin; 5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-pent-3-enyl]naphthalene-1,4-dione
Molecular FormulaC16H16O5
Molecular Weight288.30
Purity≥98 (HPLC)%
Density1.4±0.1 g/cm3
Boiling Point567.4±50.0 °C at 760 mmHg
Melting Point147ºC
Appearancesolid
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 517-89-5 |
| Catalog No. | 2A-9022447 |
| Chinese Name | 紫草素 |
| Synonyms | 5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methylpent-3-en-1-yl]-1,4-naphthoquinone; MFCD00075680; Shikonin; 5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-3-penten-1-yl]-1,4-naphthoquinone; (+)-Alkannin; 5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-pent-3-enyl]naphthalene-1,4-dione |
| Molecular Formula | C16H16O5 |
| Molecular Weight | 288.30 |
| Purity | ≥98 (HPLC) |
| Density | 1.4±0.1 g/cm3 |
| Boiling Point | 567.4±50.0 °C at 760 mmHg |
| Melting Point | 147ºC |
| Appearance | solid |
| Storage Condition | 1. Store in a cool, dry and well-ventilated wareho |
| Application | Shikonin is the main component of the Chinese herb Lithospermum chinensis. Shikonin displays various biological activities, including inhibiting TNF-α, NF-κB, and HIV-1. |
| HTC | 2914690090 |
| MDL Number | MFCD00075680 |
| SMILES | OC(CC=C(C)C)C1=CC(=O)c2c(c(ccc2O)O)C1=O |
| InChI | 1S/C16H16O5/c1-8(2)3-4-10(17)9-7-13(20)14-11(18)5-6-12(19)15(14)16(9)21/h3,5-7,10,17-19H,4H2,1-2H3 |
| InChI Key | NEZONWMXZKDMKF-UHFFFAOYSA-N |
| NACRES Code | NA.77 |
| UNSPSC | 12352200 |
| MSDS | msds/22447_1_517_89_5.pdf |
| Use of | Shikonin is a major component of a Chinese herbal medicine named zicao. Shikonin has shown various biological activities, including inhibition of TNF-α, NF-κB, HIV-1. Properties Name (R)-5,8-Dihydroxy-2-(1-hydroxy-4-methylpent-3-en-1-yl)naphthalene-1,4-dione Synonym More Synonyms Shikonine Biological Activity Description Shikonin is a major component of a Chinese herbal medicine named zicao. Shikonin has shown various biological activities, including inhibition of TNF-α, NF-κB, HIV-1. Related Catalog Signaling Pathways >> Membrane Transporter/Ion Channel >> Chloride Channel Signaling Pathways >> NF-κB >> NF-κB Signaling Pathways >> Metabolic Enzyme/Protease >> Pyruvate Kinase Signaling Pathways >> Apoptosis >> TNF Receptor Research Areas >> Cancer Natural Products >> Quinones TMEM16A chloride channel:6.5 μM (IC50) In Vivo Shikonin significantly inhibits the increase in IL-1β and TNF-α expression levels in the rat model of osteoarthritis, compare with those in the osteoarthritis group (P<0.01). The NF-κB protein expression level is significantly suppressed by Shikonin in the rat model of osteoarthritis, compare with that in the osteoarthritis group (P<0.01). The induction of the iNOS level is suppressed by treatment with Shikonin in the rat model of osteoarthritis, compare with that in the osteoarthritis group (P<0.01). The administration of Shikonin markedly weakens the up-regulation of COX-2 protein expression in the rat model of osteoarthritis, as compare with that in the osteoarthritis group (P<0.01). The elevation of caspase-3 activity is significantly reduced by Shikonin treatment in the rat model of osteoarthritis, compare with that in the osteoarthritis group (P<0.01). The downregulation of Akt phosphorylation is also significantly recovered by treatment with Shikonin in the rat model of osteoarthritis, compare with that in the osteoarthritis group (P<0.01)[5]. References [1]. Jiang Y et al. Shikonin Inhibits Intestinal Calcium-Activated Chloride Channels and Prevents Rotaviral Diarrhea. Front Pharmacol. 2016 Aug 23;7:270. [2]. Li W, et al. Shikonin Suppresses Skin Carcinogenesis via Inhibiting Cell Proliferation. PLoS One. 2015 May 11;10(5):e0126459. [3]. Yan Y, et al. Shikonin Promotes Skin Cell Proliferation and Inhibits Nuclear Factor-κB Translocation via Proteasome Inhibition In Vitro. Chin Med J (Engl). 2015 Aug 20;128(16):2228-33. [4]. Zhang FY, et al. Shikonin Inhibits the Migration and Invasion of Human Glioblastoma Cells by Targeting Phosphorylated β-Catenin and Phosphorylated PI3K/Akt: A Potential Mechanism for the Anti-Glioma Efficacy of a Traditional Chinese Herbal Medicine. Int J Mol Sci. 2015 Oct 9;16(10):23823-48. [5]. Fu D, et al. Shikonin inhibits inflammation and chondrocyte apoptosis by regulation of the PI3K/Akt signaling pathway in a rat model of osteoarthritis. Exp Ther Med. 2016 Oct;12(4):2735-2740. Chemical & Physical Properties Molecular Formula C16H16O5 Exact Mass 288.099762 PSA 94.83000 Index of Refraction 1.642 InChIKey NEZONWMXZKDMKF-SNVBAGLBSA-N Toxicological Information CHEMICAL IDENTIFICATION RTECS NUMBER : CHEMICAL NAME : 1,4-Naphthoquinone, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, (+)- CAS REGISTRY NUMBER : LAST UPDATED : DATA ITEMS CITED : MOLECULAR FORMULA : C16-H16-O5 MOLECULAR WEIGHT : WISWESSER LINE NOTATION : L66 BV EVJ CYQ2UY1&1 GQ JQ HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : NYKZAU Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. (Nippon Yakuri Gakkai, c/o Kyoto Daigaku Igakubu Yakurigaku Kyoshitsu, Konoe-cho, Yoshida, Sakyo-ku, Kyoto 606, Japan) V.40- 1944- Volume(issue)/page/year: 73,193,1977 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : TOXIC EFFECTS : Behavioral - changes in motor activity (specific assay) Behavioral - ataxia REFERENCE : NYKZAU Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. (Nippon Yakuri Gakkai, c/o Kyoto Daigaku Igakubu Yakurigaku Kyoshitsu, Konoe-cho, Yoshida, Sakyo-ku, Kyoto 606, Japan) V.40- 1944- Volume(issue)/page/year: 73,193,1977 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - rabbit DOSE/DURATION : TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : PJPHEO Pakistan Journal of Pharmacology. (c/o Univ. of Karachi, Faculty of Pharmacy, Karachi, 32, Pakistan) V.1- 1984- Volume(issue)/page/year: 3(1-2),43,1986 Safety Information Hazard Codes Xn HS Code 2914690090 Synthetic Route (R)-4-methyl-1-... 197573-96-9 Literature: Wang, Rubing; Zhou, Shanshan; Jiang, Hudagula; Zheng, Xiaogang; Zhou, Wen; Li, Shaoshun European Journal of Organic Chemistry, 2012 , # 7 p. 1373 - 1379 (R)-4-methyl-1-... 206996-08-9 Literature: Nicolaou; Hepworth, David Angewandte Chemie - International Edition, 1998 , vol. 37, # 6 p. 839 - 841 4-BROMONAPHTHO[... 88051-30-3 Literature: Nicolaou; Hepworth, David Angewandte Chemie - International Edition, 1998 , vol. 37, # 6 p. 839 - 841 Precursor & DownStream Precursor 7 CAS#:206996-08-9 (R)-4-methyl-1-... CAS#:88051-30-3 4-BROMONAPHTHO[... CAS#:88051-28-9 NAPHTHO[1,8-DE:... CAS#:88818-28-4 2-SULFO-1,4-BEN... DownStream 2 CAS#:24502-78-1 Acetylshikonin CAS#:517-90-8 5,8-dihydroxy-2... |
| Tax Rebate | 9.0% |
| Supervision | None MFN tariff: 5.5% Ordinary tariff: 30.0% |
| Transport Info | Product name: Shikonin |
| Related Products in Specialty Chemicals | ||
|---|---|---|
| Taurochenodeoxycholic acid | 516-35-8 | 2A-9022439 |
| 2-Acetylbutyrolactone | 517-23-7 | 2A-9022442 |
| Hematoxylin | 517-28-2 | 2A-0202046 |
| Rubrene | 517-51-1 | 2A-9022445 |
| Alkannin | 517-88-4 | 2A-9022446 |
| Evodiamine | 518-17-2 | 2A-9022448 |
| Dimethoxanate hydrochloride | 518-63-8 | 2A-9022452 |
| Dimidium bromide | 518-67-2 | 2A-9022453 |
| Corydaline | 518-69-4 | 2A-9022454 |
| Cycleanine | 518-94-5 | 2A-9022456 |
| Browse all Specialty Chemicals products » | ||
Phone:
630-322-8886
630-322-8887
Email:
Office Locations:
Chicago, IL, USA
San Francisco, CA, USA
EN
SDS